Travel

The Chicago Guide

Chicago is easy to love. First, there’s the famous Midwestern charm, which can’t be overstated and seems genetically wired in its inhabitants. People are just really nice here. Then, of course, there are world class museums, parks, parks, parks everywhere you look, and so many great restaurants we’ve barely made a dent in our checklist. And every year, it just gets better. Formerly off-the-beaten path neighborhoods, like Logan Square and Bucktown, are now front-and-center when it comes to Chicago’s new crop of hip watering holes, while old school haunts, like The Peninsula (one of GP’s favorites), are getting fresh, modern makeovers. As much as we love sharing everything new, though, we’re also rediscovering cultural institutions, shops, and restaurants that deserve newfound attention. It’s this uniquely Chicago mix, after all, that makes this city so endlessly exciting.

Over a century ago, this Michigan Avenue landmark served as home base of the Chicago Athletic Association. The building had been vacant since 1997, so it was a pretty big deal when design firm Roman and Williams stepped in to re-imagine the massive building as a slick 241-room hotel. Sport is still a prominent theme here, as evidenced by a tricked out game room and walls of museum quality athletic memorabilia. And while the stained glass windows, grand ballroom, and general clubbiness were left intact, the brass lighting fixtures and leather furniture (both in-room and throughout the hotel) are welcome additions. There's also the sexy rooftop restaurant, Cindy's, a Shake Shack, and three more places to eat and drink. Incidentally, the cozy library at Cindy's is an excellent place to host a private event—it doesn't feel at all like a corporate hotel space, and the views of Lake Michigan are jaw-dropping.

Scoring a membership here is like hitting the Soho House jackpot: There’s a rooftop pool, a killer house restaurant (and a separate white-tablecloth option), Cowshed spa, tricked-out gym with boxing ring, and a 40-room hotel. Including the two public restaurants on the ground floor (Chicken Shop and Pizza East), this is the largest space on the roster. And while it’s been a long time coming (nine years since Nick Jones first set his sights on Chi town), this outpost looks and feels like it fits right in with its cool West Loop surroundings.

This is easily the hippest hotel in town, and at only 6 rooms strong, it’s also the tiniest. But what it lacks in size and fancy amenities (there’s no concierge or room service) it totally makes up for in fun and food. For one thing, the open-plan rooms are exceptionally designed (terrariums, freestanding tubs, custom furniture handmade by the owners) with hilarious little details like vintage Fisher Price tape decks and PBR in the mini fridge. The guesthouse sits directly on top of its namesake Michelin star restaurant, which means that wild boar sloppy joes and over 150 varieties of whiskey are literally steps away. Understandably evenings tend to get rowdy, so keep that in mind when booking.

Only a few years old, this 300+ room hotel takes up the first 13 floors of the Mies van der Rohe-designed IBM building (it’s actually the architect’s final work) but feels more like a boutique operation rather than a corporate-y behemoth. That said, it’s well equipped to host both business and leisure-minded travelers: spacious rooms, a choice of on-site restaurants, and a killer spa. It also offers all the thoughtful extras one might expect from a Langham, including afternoon tea service and a mini fleet of the signature pink taxis.

The Waldorf’s massive, elegantly appointed guestrooms—a good portion of which have working fireplaces—are just one of the many reasons why we chose it as our home away from home during the Chicago goop pop (it actually used to be the Elysian, another goop fave). Here, a heated porte-cochère (a godsend during those brutal Midwestern winters) gives you the sense that comfort is taken very seriously before you even step through the doors. Balsan, the on-site bistro, has a solid selection of classic American fare (burgers, salads, and super fresh oysters), so leaving the grounds for a great market-driven meal isn’t a necessity.

We don’t say this much—or ever—but: The Peninsula is maybe our favorite urban hotel in the entire country. It was recently renovated, which, in this case, means new custom artwork in the guest rooms (including silk floral wall prints), tablet technology for controlling everything (lights, curtains, room service) by touchpad, and a new cocktail lounge, Z Bar, perched high above Michigan Avenue, where drinks are made tableside on a roving cart. Sipping an Old Fashioned here while soaking in the rooftop views before heading to your room and falling asleep on Pretesi linens in one of the Peninsula’s supremely comfortable beds…this is the perfect Chicago evening.

Located in the hub of the art and design district, the Palomar is a modern, pet-friendly, eco-friendly, organic-oriented hotel that caters to active city visitors. The hotel organizes fun group exercise classes that include guided runs along Lake Michigan and ballet barre workouts on the hotel’s sundeck. Other novel perks are the in-room massages and yoga sessions. And, if you travel with your pets, you’ll be pleased with all the amenities that they’ll enjoy. Sable, one of the best bars around, is just down the stairs.

Simply put, this downtown hotel's proximity to some of the city's best sites can't be beat: Millennium Park, The Museum of Contemporary Art, and Michigan Avenue are all just steps away. It offers all the comforts and amenities you'd need (bike rentals, a great gym), in addition to a sleek, modern design that makes it nothing short of a city oasis.

The second Freehand outpost (the first is in Miami) refers to itself as a hotel-slash-hostel, meaning they've made their beautifully appointed shared and private rooms exceptionally tourist and wallet-friendly. Designed by goop favorites Roman and Williams, it's all understated, eclectic comfort through and through: Public areas are set up like living rooms with a cafe and bar right on property—that's all in addition to a 24/7 communal kitchen.

Perched inside the only skyscraper for miles, this new Wicker Park hotel not only boasts killer views of downtown, it's located on one of the best intersections in the city—at the corner Damen, Milwaukee and North Avenues, it's just steps from Big Star, Dove’s Luncheonette, Eskell Boutique, and the Damen Blue Line stop. The building itself is an art deco jewel that preserves much of the charm of its 1920s design, and its triangular footprint means each of the hotel's 69 rooms are filled with plenty of light. Their 13th-floor rooftop lounge, Up & Up, is a great place to grab a drink, too.

In Chicago's buzzy and rapidly gentrifying West Loop, Ace Hotel has set up shop right across from Google's Midwest HQ. Fittingly, the 159-room property is a nod to the city's strong architectural history having partnered with LA-based Commune design studio to thoughtfully marry both utility and craftsmanship. Taking inspiration from Mies Van der Rohe and Frank Lloyd Wright, the hotel expertly mixes warm woods, clean lines, and rich textures. Commune and Ace also tapped Chicago's Volume Gallery, which specializes in American Craft, to collaborate on a series of pieces specifically for the hotel by emerging and mid-career area artists. In the guest rooms, the low-slung plywood furniture references Mid-century design with pops of blue, greens, and grays and geometric patterns. (One of our favorite rooms is the Loft, a 545-plus square foot space, where a turntable and selection of curated vinyl and an acoustic Martin guitar are also on offer.) Downstairs, Stumptown Coffee set up shop just off the lobby —it's their first location in the Midwest—making for an ideal pit stop before you explore the neighborhood by foot.

This boutique hotel feels at once like an urban loft and a cozy cabin, combining rich colors and exposed brick with stellar views of Lake Michigan and the Chicago skyline. Its Gold Coast location means it's just a walk away from shopping and dining on the Magnificent Mile (and legendary pizza from Lou Malnati's), though the admired Osteria Nico downstairs means you don't even have to leave the hotel for Italian with a view. Just as enticing are the modern rooms themselves, featuring velvet seating and Brooklyn-made D.S. & Durga toiletries. If you do decide to change out of the insanely comfortable robes and venture outdoors, though, take advantage of the hotel's complimentary offsite car service.